Benzyl chloroformate → 1-N-Boc-4-(N-cbz-aminomethyl)piperidine

HRID 1826596Notes

Reaction equation

HRID 1826596 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]>C1COCC1.O.[OH-].[Na+]>[CH2:20]([O:19][C:17]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 7368171-Boc-4-(aminomethyl)piperidine

Product 1

HCID 117920261-N-Boc-4-(N-cbz-aminomethyl)piperidineYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-aminomethyl-1-Boc-piperidine (5.00 g, 23.4 mmol) in THF (60 mL), water (14 mL) and 5 N NaOH (46 mL) was treated with benzyl chloroformate. After 12 h, the mixture was partitioned between EtOAc and water and the aqueous phase washed with EtOAc (3×). The combined extracts were washed with water, brine and concentrated to afford 7.6 g (93%) of the title compound which was used without further purification.

Workup

  1. customthe mixture was partitioned between EtOAc and water
  2. washthe aqueous phase washed with EtOAc (3×)
  3. washThe combined extracts were washed with water, brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ecd4dccd05cf454180dc560f86a52be8
Source dataset
uspto-grants-2006_05
Patent number
US07053078B2

Reaction notes

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